WordPress succeeded by going where the money wasn't

How did WordPress win over Movable Type? Majordomo has a good review of Six Apart’s strategic weaknesses and errors, and how WordPress/Automattic exploited each of them.
In my opinion, Six Apart’s biggest error was its choice of focusing on the enterprise market just as blogging was poised to go mainstream. This was an understandable mistake. They had investors to satisfy (not necessarily a bad thing) and there was no clear path to profitability for a software platform in the mass blogging market.
This lead directly to the Six Apart’s disastrous change in their license, which created WordPress’s moment of opportunity.
I was a happy Movable Type user at the time, but I was moving in other directions. I adopted Expression Engine for my next site, because MT didn’t have the membership management tools I needed. By the time I was ready to refocus my efforts on my MT site (MediaSavvy) in 2009, it was actually easier (by which I mean “possible”) to move it from an old version to MT to the latest WordPress than it was to upgrade to the latest version of Movable Type. Things had changed a lot in four years and the game was over.
The next time you justify a strategic decision by saying “That’s where money is”, you should remember that Willie Sutton was not a brilliant strategist.